CA3086092A1

CA3086092A1 - Novel galactoside inhibitor of galectins

Novel galactoside inhibitor of galectins Download PDF

Info

Publication number: CA3086092A1
Authority: CA; Canada
Prior art keywords: deoxy; thio; galactopyranoside; triazol; mmol
Prior art date: 2018-01-10
Legal status : Pending

Application number

CA3086092A

Other languages

English (en)

French (fr)

Inventor

Fredrik Zetterberg

Current Assignee

Galecto Biotech AB

Original Assignee

Galecto Biotech AB

Priority date

2018-01-10

Filing date

2019-01-09

Publication date

2019-07-18

2019-01-09 Application filed by Galecto Biotech AB filed Critical Galecto Biotech AB

2019-07-18 Publication of CA3086092A1 publication Critical patent/CA3086092A1/en

Status Pending legal-status Critical Current

Links

102000007563 Galectins Human genes 0.000 title abstract description 47
108010046569 Galectins Proteins 0.000 title abstract description 47
239000003112 inhibitor Substances 0.000 title description 30
150000008195 galaktosides Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 254
108010001498 Galectin 1 Proteins 0.000 claims abstract description 56
238000000034 method Methods 0.000 claims abstract description 43
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims abstract description 16
241000124008 Mammalia Species 0.000 claims abstract description 15
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
230000027455 binding Effects 0.000 claims abstract description 11
239000003446 ligand Substances 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
125000001425 triazolyl group Chemical group 0.000 claims abstract description 6
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
150000003214 pyranose derivatives Chemical group 0.000 claims abstract description 4
102000000795 Galectin 1 Human genes 0.000 claims abstract 3
-1 D-galactopyranose compound Chemical class 0.000 claims description 120
229910052736 halogen Inorganic materials 0.000 claims description 61
150000002367 halogens Chemical class 0.000 claims description 61
125000000217 alkyl group Chemical group 0.000 claims description 57
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 45
206010028980 Neoplasm Diseases 0.000 claims description 45
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238000011282 treatment Methods 0.000 claims description 23
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239000001257 hydrogen Substances 0.000 claims description 21
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125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 2
239000000243 solution Substances 0.000 description 108
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 104
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239000012267 brine Substances 0.000 description 35
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 35
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
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WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 20
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